JP3143877B2 - (s)−ビニル及びアレニルgabaの製法 - Google Patents
(s)−ビニル及びアレニルgabaの製法Info
- Publication number
- JP3143877B2 JP3143877B2 JP03352847A JP35284791A JP3143877B2 JP 3143877 B2 JP3143877 B2 JP 3143877B2 JP 03352847 A JP03352847 A JP 03352847A JP 35284791 A JP35284791 A JP 35284791A JP 3143877 B2 JP3143877 B2 JP 3143877B2
- Authority
- JP
- Japan
- Prior art keywords
- solution
- formula
- mmol
- chloride
- added
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 18
- -1 allenyl GABA Chemical compound 0.000 title abstract description 43
- 229960003692 gamma aminobutyric acid Drugs 0.000 title abstract description 9
- 229920002554 vinyl polymer Polymers 0.000 title 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 238000006460 hydrolysis reaction Methods 0.000 claims description 26
- 230000007062 hydrolysis Effects 0.000 claims description 20
- 238000005917 acylation reaction Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000004040 pyrrolidinones Chemical class 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims 3
- OYVDXEVJHXWJAE-RXMQYKEDSA-N (5s)-5-ethenylpyrrolidin-2-one Chemical compound C=C[C@@H]1CCC(=O)N1 OYVDXEVJHXWJAE-RXMQYKEDSA-N 0.000 abstract description 14
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 2
- 230000000707 stereoselective effect Effects 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 99
- 239000000243 solution Substances 0.000 description 80
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 71
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 238000005481 NMR spectroscopy Methods 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 239000011541 reaction mixture Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- 239000000741 silica gel Substances 0.000 description 29
- 229910002027 silica gel Inorganic materials 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 235000019439 ethyl acetate Nutrition 0.000 description 24
- 150000001450 anions Chemical class 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- OYVDXEVJHXWJAE-UHFFFAOYSA-N 5-ethenylpyrrolidin-2-one Chemical compound C=CC1CCC(=O)N1 OYVDXEVJHXWJAE-UHFFFAOYSA-N 0.000 description 17
- 239000000284 extract Substances 0.000 description 16
- 238000002390 rotary evaporation Methods 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000012141 concentrate Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 239000002245 particle Substances 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 11
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 230000010933 acylation Effects 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 238000003818 flash chromatography Methods 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- ZQHHVFKRZCLJNC-ZETCQYMHSA-N (2s)-2-methyl-3-oxo-3-phenylpropanoyl chloride Chemical class ClC(=O)[C@@H](C)C(=O)C1=CC=CC=C1 ZQHHVFKRZCLJNC-ZETCQYMHSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- JAAUMNFJPMIUQM-LLVKDONJSA-N (2r)-2-(2,4-ditert-butylphenoxy)propanoyl chloride Chemical class ClC(=O)[C@@H](C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JAAUMNFJPMIUQM-LLVKDONJSA-N 0.000 description 6
- KGUNHUZKDVVKPH-SNVBAGLBSA-N (2r)-2-(3,5-ditert-butyl-4-hydroxyphenyl)propanethioyl chloride Chemical class ClC(=S)[C@H](C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KGUNHUZKDVVKPH-SNVBAGLBSA-N 0.000 description 6
- OFDVSAVRQDOJSU-LLVKDONJSA-N (2r)-2-(3,5-ditert-butylphenoxy)propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1 OFDVSAVRQDOJSU-LLVKDONJSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- CVSPHBJKUVGOMD-LLVKDONJSA-N (2r)-2-(2,4-ditert-butylphenoxy)propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C CVSPHBJKUVGOMD-LLVKDONJSA-N 0.000 description 5
- UXEQIBCSCBKRPL-LLVKDONJSA-N (2r)-2-(3,5-ditert-butylphenoxy)propanoyl chloride Chemical class ClC(=O)[C@@H](C)OC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1 UXEQIBCSCBKRPL-LLVKDONJSA-N 0.000 description 5
- VMEPJNQRTTXULS-ZDUSSCGKSA-N (2s)-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl chloride Chemical compound CC(C)(C)[Si](C)(C)O[C@H](C(Cl)=O)CC1=CC=CC=C1 VMEPJNQRTTXULS-ZDUSSCGKSA-N 0.000 description 5
- XEYSXLKRBATYDV-ZCFIWIBFSA-N (5s)-5-propa-1,2-dienylpyrrolidin-2-one Chemical compound C=C=C[C@@H]1CCC(=O)N1 XEYSXLKRBATYDV-ZCFIWIBFSA-N 0.000 description 5
- 239000002178 crystalline material Substances 0.000 description 5
- 238000010511 deprotection reaction Methods 0.000 description 5
- RAWGHPXIJSCHFZ-VIFPVBQESA-N ethyl (2s)-2-methyl-3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)[C@@H](C)C(=O)C1=CC=CC=C1 RAWGHPXIJSCHFZ-VIFPVBQESA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- BYSFONKODLHDKK-SNVBAGLBSA-N (2r)-2-(3,5-ditert-butyl-4-hydroxyphenyl)propanethioic s-acid Chemical compound SC(=O)[C@H](C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BYSFONKODLHDKK-SNVBAGLBSA-N 0.000 description 4
- AWYZUBUIFKMOFY-ZETCQYMHSA-N (2s)-2-[tert-butyl(dimethyl)silyl]oxypropanoyl chloride Chemical compound ClC(=O)[C@H](C)O[Si](C)(C)C(C)(C)C AWYZUBUIFKMOFY-ZETCQYMHSA-N 0.000 description 4
- XWILORJMRMFKPM-ZCFIWIBFSA-N (4s)-4-aminohepta-5,6-dienoic acid Chemical compound C=C=C[C@@H](N)CCC(O)=O XWILORJMRMFKPM-ZCFIWIBFSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 4
- 238000006073 displacement reaction Methods 0.000 description 4
- LZCLXQDLBQLTDK-BYPYZUCNSA-N ethyl (2S)-lactate Chemical compound CCOC(=O)[C@H](C)O LZCLXQDLBQLTDK-BYPYZUCNSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- SJJHBCILZGFCME-WCQYABFASA-N (2s)-1-[(2s)-2-ethenyl-5-oxopyrrolidin-1-yl]-2-methyl-3-phenylpropane-1,3-dione Chemical compound O=C([C@@H](C)C(=O)C=1C=CC=CC=1)N1[C@H](C=C)CCC1=O SJJHBCILZGFCME-WCQYABFASA-N 0.000 description 3
- FVXFWBAJDYXSHV-NVXWUHKLSA-N (5s)-1-[(2r)-2-(2,4-ditert-butylphenoxy)propanoyl]-5-ethenylpyrrolidin-2-one Chemical compound O([C@H](C)C(=O)N1C(CC[C@H]1C=C)=O)C1=CC=C(C(C)(C)C)C=C1C(C)(C)C FVXFWBAJDYXSHV-NVXWUHKLSA-N 0.000 description 3
- HNVAVUFFJZRPAD-MAUKXSAKSA-N (5s)-1-[(2s)-2-(3,5-ditert-butylphenoxy)propanoyl]-5-ethenylpyrrolidin-2-one Chemical compound O([C@@H](C)C(=O)N1C(CC[C@H]1C=C)=O)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1 HNVAVUFFJZRPAD-MAUKXSAKSA-N 0.000 description 3
- XEYSXLKRBATYDV-UHFFFAOYSA-N 5-propa-1,2-dienylpyrrolidin-2-one Chemical compound C=C=CC1CCC(=O)N1 XEYSXLKRBATYDV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000006181 N-acylation Effects 0.000 description 3
- VULIHENHKGDFAB-UHFFFAOYSA-N Pterolactam Chemical compound COC1CCC(=O)N1 VULIHENHKGDFAB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 3
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002893 slag Substances 0.000 description 3
- PJDFLNIOAUIZSL-UHFFFAOYSA-N vigabatrin Chemical compound C=CC(N)CCC(O)=O PJDFLNIOAUIZSL-UHFFFAOYSA-N 0.000 description 3
- PJDFLNIOAUIZSL-RXMQYKEDSA-N (4s)-4-azaniumylhex-5-enoate Chemical compound C=C[C@@H](N)CCC(O)=O PJDFLNIOAUIZSL-RXMQYKEDSA-N 0.000 description 2
- BABNLXYNWLYICF-GDBMZVCRSA-N (5s)-1-[(2r)-2-(3,5-ditert-butyl-4-hydroxyphenyl)propanethioyl]-5-ethenylpyrrolidin-2-one Chemical compound S=C([C@H](C)C=1C=C(C(O)=C(C=1)C(C)(C)C)C(C)(C)C)N1[C@H](C=C)CCC1=O BABNLXYNWLYICF-GDBMZVCRSA-N 0.000 description 2
- XKPNHROVKBKJLM-MSOLQXFVSA-N (5s)-1-[(2s)-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]-5-ethenylpyrrolidin-2-one Chemical compound C([C@H](O[Si](C)(C)C(C)(C)C)C(=O)N1C(CC[C@H]1C=C)=O)C1=CC=CC=C1 XKPNHROVKBKJLM-MSOLQXFVSA-N 0.000 description 2
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003862 amino acid derivatives Chemical class 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 229940017219 methyl propionate Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000006884 silylation reaction Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
- XNRVLTFHQDPFIP-NWDGAFQWSA-N (5s)-1-[(2s)-2-[tert-butyl(dimethyl)silyl]oxypropanoyl]-5-ethenylpyrrolidin-2-one Chemical compound CC(C)(C)[Si](C)(C)O[C@@H](C)C(=O)N1[C@H](C=C)CCC1=O XNRVLTFHQDPFIP-NWDGAFQWSA-N 0.000 description 1
- NFVMNXZFSKGLDR-UHFFFAOYSA-N 2,6-ditert-butyl-4-sulfanylphenol Chemical compound CC(C)(C)C1=CC(S)=CC(C(C)(C)C)=C1O NFVMNXZFSKGLDR-UHFFFAOYSA-N 0.000 description 1
- BYSFONKODLHDKK-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)propanethioic s-acid Chemical compound SC(=O)C(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BYSFONKODLHDKK-UHFFFAOYSA-N 0.000 description 1
- NPSWHDAHNWWMEG-UHFFFAOYSA-N 2-aminohex-5-enoic acid Chemical compound OC(=O)C(N)CCC=C NPSWHDAHNWWMEG-UHFFFAOYSA-N 0.000 description 1
- XNVAUNOSRHPXCY-UHFFFAOYSA-N 2-ethenylpyrrolidine Chemical compound C=CC1CCCN1 XNVAUNOSRHPXCY-UHFFFAOYSA-N 0.000 description 1
- ZDWSNKPLZUXBPE-UHFFFAOYSA-N 3,5-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1 ZDWSNKPLZUXBPE-UHFFFAOYSA-N 0.000 description 1
- MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 1
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NYJFSHJXNLBPAX-UHFFFAOYSA-N chloro hypochlorite;n,n-dimethylformamide Chemical compound ClOCl.CN(C)C=O NYJFSHJXNLBPAX-UHFFFAOYSA-N 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- RAWGHPXIJSCHFZ-UHFFFAOYSA-N ethyl 2-methyl-3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)C(C)C(=O)C1=CC=CC=C1 RAWGHPXIJSCHFZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-VKHMYHEASA-N methyl (S)-lactate Chemical compound COC(=O)[C@H](C)O LPEKGGXMPWTOCB-VKHMYHEASA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical group CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- ULYLMHUHFUQKOE-UHFFFAOYSA-N trimethyl(prop-2-ynyl)silane Chemical compound C[Si](C)(C)CC#C ULYLMHUHFUQKOE-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/22—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from lactams, cyclic ketones or cyclic oximes, e.g. by reactions involving Beckmann rearrangement
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/30—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US62873890A | 1990-12-17 | 1990-12-17 | |
US07/628,738 | 1990-12-17 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH04334364A JPH04334364A (ja) | 1992-11-20 |
JP3143877B2 true JP3143877B2 (ja) | 2001-03-07 |
Family
ID=24520094
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP03352847A Expired - Lifetime JP3143877B2 (ja) | 1990-12-17 | 1991-12-17 | (s)−ビニル及びアレニルgabaの製法 |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP0492350B1 (de) |
JP (1) | JP3143877B2 (de) |
KR (1) | KR920012021A (de) |
AT (1) | ATE159246T1 (de) |
AU (2) | AU644919B2 (de) |
CA (1) | CA2057699C (de) |
DE (1) | DE69127960T2 (de) |
DK (1) | DK0492350T3 (de) |
ES (1) | ES2110974T3 (de) |
GR (1) | GR3025831T3 (de) |
HU (1) | HU218793B (de) |
IE (1) | IE914371A1 (de) |
IL (1) | IL100360A (de) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU644919B2 (en) * | 1990-12-17 | 1993-12-23 | Aventisub Ii Inc. | Process for the production of (S)-vinyl and allenyl gaba |
JP3671252B2 (ja) * | 1993-06-23 | 2005-07-13 | メレルファーマスーティカルズ インコーポレイテッド | (s)−4−アミノ−ヘプタ−5,6−ジエン酸とその中間体類の製法 |
ITMI991330A1 (it) * | 1999-06-15 | 2000-12-15 | Isagro Spa | Processo per la preparazione di fungicidi otticamente attivi costituiti da n-acil derivati del metil n-(2,6-dimetilfenil)-d-alaninato |
CN110713440B (zh) * | 2018-07-11 | 2022-01-25 | 武汉武药科技有限公司 | 一种氨己烯酸的制备方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3960927A (en) * | 1975-03-18 | 1976-06-01 | Richardson-Merrell Inc. | Olefinic derivatives of amino acids |
US3959356A (en) * | 1975-03-18 | 1976-05-25 | Richardson-Merrell Inc. | Acetylene derivatives of amino acids |
GB2120244B (en) * | 1982-05-17 | 1985-05-01 | Merrell Toraude & Co | Aminoalkadiene derivative |
GB2133002B (en) * | 1982-12-30 | 1986-01-29 | Merrell Toraude & Co | Process for preparing 4-amino-5-hexenoic acid |
CA1252477A (en) * | 1983-07-07 | 1989-04-11 | Alexander Krantz | .gamma.-ALLENYL-.gamma.-AMINOBUTYRIC ACIDS |
US4912232A (en) * | 1983-10-14 | 1990-03-27 | Dow Chemical Company | Preparation of N-hydrocarbylcarbonyl-5-(1-hydrocarbylcarbonyloxy)hydrocarbyl-pyrrolidin-2-one |
US4873336A (en) * | 1988-03-28 | 1989-10-10 | Gaf Corporation | Process for the preparation of N-vinyl lactams |
EP0342613B1 (de) * | 1988-05-20 | 1992-11-11 | ZAMBON GROUP S.p.A. | Verbindungen mit zentraler analgetischer Verwendung, Verfahren zu ihrer Herstellung und Arzneimittel die sie enthalten |
AU644919B2 (en) * | 1990-12-17 | 1993-12-23 | Aventisub Ii Inc. | Process for the production of (S)-vinyl and allenyl gaba |
-
1991
- 1991-12-12 AU AU89635/91A patent/AU644919B2/en not_active Expired
- 1991-12-12 IL IL10036091A patent/IL100360A/en not_active IP Right Cessation
- 1991-12-16 DK DK91121554.9T patent/DK0492350T3/da active
- 1991-12-16 HU HU969/91A patent/HU218793B/hu unknown
- 1991-12-16 IE IE437191A patent/IE914371A1/en not_active IP Right Cessation
- 1991-12-16 ES ES91121554T patent/ES2110974T3/es not_active Expired - Lifetime
- 1991-12-16 EP EP91121554A patent/EP0492350B1/de not_active Expired - Lifetime
- 1991-12-16 CA CA002057699A patent/CA2057699C/en not_active Expired - Lifetime
- 1991-12-16 DE DE69127960T patent/DE69127960T2/de not_active Expired - Lifetime
- 1991-12-16 AT AT91121554T patent/ATE159246T1/de not_active IP Right Cessation
- 1991-12-17 KR KR1019910023189A patent/KR920012021A/ko not_active Application Discontinuation
- 1991-12-17 JP JP03352847A patent/JP3143877B2/ja not_active Expired - Lifetime
-
1994
- 1994-01-21 AU AU53900/94A patent/AU658538B2/en not_active Expired
-
1998
- 1998-01-07 GR GR980400006T patent/GR3025831T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
DE69127960D1 (de) | 1997-11-20 |
HU913969D0 (en) | 1992-02-28 |
CA2057699A1 (en) | 1992-06-18 |
AU5390094A (en) | 1994-03-17 |
ES2110974T3 (es) | 1998-03-01 |
IL100360A (en) | 1998-08-16 |
DE69127960T2 (de) | 1998-03-05 |
IL100360A0 (en) | 1992-09-06 |
AU8963591A (en) | 1992-06-18 |
AU644919B2 (en) | 1993-12-23 |
KR920012021A (ko) | 1992-07-25 |
IE914371A1 (en) | 1992-06-17 |
HU218793B (hu) | 2000-12-28 |
ATE159246T1 (de) | 1997-11-15 |
HUT63829A (en) | 1993-10-28 |
EP0492350B1 (de) | 1997-10-15 |
CA2057699C (en) | 2002-10-29 |
EP0492350A1 (de) | 1992-07-01 |
GR3025831T3 (en) | 1998-04-30 |
JPH04334364A (ja) | 1992-11-20 |
DK0492350T3 (da) | 1998-01-26 |
AU658538B2 (en) | 1995-04-13 |
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